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Updated: Mar 17, 2026

Isolating Free Carbenes, their Mixed Dimers and Organic Radicals
Published on: April 19, 2019
Reactions of a cerium(iii) amide with heteroallenes: insertion, silyl-migration and de-insertion
Haolin Yin1, Patrick J Carroll1, Eric J Schelter1
1P. Roy and Diana T. Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, 231 S. 34th Street, Philadelphia, Pennsylvania 19104, USA. schelter@sas.upenn.edu.
Abstract:
Reactions of Ce[N(SiMe3)Ph(F)]3 (-Ph(F) = pentafluorophenyl) toward small molecules of the type E1[double bond, length as m-dash]C[double bond, length as m-dash]E2 (E1, E2 = O, S, NR), including carbon disulfide, carbodiimide, carbon dioxide, isocyanate and isothiocyanate are reported, resulting in distinct products, including cerium(iii) dithiocarbamate, cerium(iii) guanidinate, isocyanates and unsymmetric carbodiimides. These reactions were rationalized as three consecutive stages of the same reaction pathway: insertion, silyl-migration and de-insertion.
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